Trisubstituted 1,3,5-triazine-2,4,6-triones

ABSTRACT

Fungicidally active trisubstituted 1,3,5-triazine-2,4,6-trione of the formula   &lt;IMAGE&gt;   in which Ar represents optionally substituted aryl, R1 represents an optionally substituted aliphatic or cycloaliphatic radical and R2 represents an optionally substituted aliphatic radical.

This is a continuation-in-part of Application Ser. No. 050,981, filedMay 15, 1987, now pending.

The invention relates to new trisubstituted1,3,5-triazine-2,4,6-triones, processes for their preparation and theiruse for combating pests, in particular as fungicides.

It has already been disclosed that 2-arylamino-4,6-dichloro-s-triazines, such as, for example,4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine, have fungicidalproperties (compare DAS (German Published Specification) No. 1,670,675).However, the selective fungicidal activity of these substances islimited to only a few fungi and is not always adequate.

New trisubstituted 1,3,5-triazine-2,4,6-triones of the general formula(I) ##STR2## in which Ar represents optionally substituted aryl,

R¹ represents an optionally substituted aliphatic or cycloaliphaticradical and

R² represents an optionally substituted aliphatic radical,

have been found.

It has furthermore been found that the new trisubstituted1,3,5-triazine-2,4,6-triones of the formula (I) ##STR3## in which Arrepresents optionally substituted aryl,

R¹ represents an optionally substituted aliphatic or cycloaliphaticradical and

R² represents an optionally substituted aliphatic radical are obtainedeither by a process in which

(a) 1-aryl-3-alkyl-1,3,5-triazine-2,4,6-triones of the general formula(II) ##STR4## in which Ar and R¹ have the abovementioned meanings, arereacted with a compounds of the general formula (III)

    R.sup.2 --X                                                (III)

in which

R² has the abovementioned meaning and

X denotes a leaving group, such as, for example, halogen or sulphate,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent, or by a process in which

(b) in the case where R² denotes alkyl, N,N'-disubstituted ureas of thegeneral formula (IV)

    Ar--NH--CO--NH--R.sup.1                                    (IV)

in which Ar and R¹ have the abovementioned meanings, are reacted with abischlorocarbonylamine of the general formula ##STR5## If appropriate inthe presence of a diluent and if appropriate in the presence of anacid-binding agent, or by a process in which

(c) in the case where R² has the meaning given, with the exception ofcyanoalkyl, N,N'-dialkylureas of the general formula (VI)

    R.sup.1 --NH--CO--NH--R.sup.2                              (VI)

in which

R¹ has the abovementioned meaning and

R² has the meaning given, excluding cyanoalkyl,

are reacted with compounds of the general formula (VII) ##STR6## inwhich Ar has the abovementioned meaning.

Finally, it has been found that the new trisubstituted1,3,5-triazine-2,4,6-triones of the formula (I) have very goodbiological properties and are suitable, above all, for selectivelycombating harmful fungi in rice.

It is to be described as exceptionally surprising that the substancesaccording to the invention exhibit a better biological activity thanknown compounds of the prior art of the same type of action and/orstructurally similar compounds.

Formula (I) provides a general definition of the trisubstituted1,3,5-triazine-2,4,6-triones according to the invention. Preferredcompounds of the formula (I) are those

in which

Ar represents phenyl, which is optionally mono-, di-, tri-, tetra- orpentasubstituted by identical or different substituents from the groupcomprising halogen, alkyl with 1 to 4 carbon atoms, halogenoalkyl with 1to 4 carbon atoms and 1 to 5 identical or different halogen atoms,alkoxy with 1 to 4 carbon atoms, halogenoalkoxy with 1 to 4 carbon atomsand 1 to 5 identical or different halogen atoms, alkythio with 1 to 4carbon atoms, and halogenoalkylthio with 1 to 4 carbon atoms and 1 to 5identical or different hologen atoms, or represents halogenosulphonyl,or represents dialkylamino with identical or different straight-chain orbranched alkyl radicals with in each case 1 to 4 carbon atoms and/ornitro,

R¹ represents straight-chain or branched alkyl which has 1 to 12 carbonatoms and is optionally mono- or polysubstituted by identical ordifferent substituents from the group comprising halogen, alkoxy with 1to 3 carbon atoms, halogenoalkoxy with 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, alkylthio with 1 to 3 carbonatoms, halogenoalkylthio with 1 or 2 carbon atoms and 1 to 5 identicalor different halogen atoms and furyl and phenyl, which can likewise bemono-, di-, tri-, tetra-, or pentasubstituted by identical or differenthalogen atoms; or represents cycloalkyl which has 3 to 8 carbon atomsand is optionally mono-, di-, tri-, tetra-, penta- or hexasubstituted byidentical or different substitutents from the group comprising halogen,alkyl with 1 to 4 carbon atoms, alkoxy with 1 3 carbon atoms,halogenoalkoxy with 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, alkylthio with 1 to 3 carbon atoms andhalogenoalkylthio with 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, and

R² represents alkyl with 1 to 4 carbon atoms, alkenyl with 3 to 5 carbonatoms, alkinyl with 3 to 5 carbon atoms, alkoxyalkyl with in each case 1to 3 carbon atoms in the alkoxy part and in the alkyl part,alkylthioalkyl with in each case 1 to 3 carbon atoms in the alkylthiopart and in the alkyl part or alkoxycarbonylalkyl with 1 to 3 carbonatoms in the alkoxy part and 2 or 3 carbon atoms in the alkyl part, orrepresents cyanoalkyl with 1 to 5 carbon atoms in the alkyl part.

Particularly preferred compounds of the formula (I) are those

in which

Ar represents phenyl which is optionally mono-, di-, tri- ortetrasubstituted by identical or different substituents from the groupcomprising fluorine, chlorine, bromine, alkyl with 1 to 3 carbon atoms,halogenoalkyl with 1 or 2 carbon atoms and 1 to 5 chlorine and/orfluorine atoms, alkoxy with 1 to 3 carbon atoms, halogenoalkoxy with 1or 2 carbon atoms and 1 to 5 chlorine and/or fluorine atoms, alkylthiowith 1 or 2 carbon atoms, halogenoalkylthio with 1 or 2 carbon atoms and1 to 5 chlorine and/or fluorine atoms, fluorosulphonyl, dialkylaminowith identical or different straight-chain or branched alkyl radicalswith in each case 1 to 3 carbon atoms and/or nitro,

R¹ represents straight-chain or branched alkyl which has 1 to 12 carbonatoms and can be mono-, di-, or trisubstituted by identical or differentsubstituents from the group comprising fluorine, chlorine, alkoxy with 1or 2 carbon atoms, halogenoalkoxy with 1 or 2 carbon atoms and 1 to 3chlorine and/or fluorine atoms, alkylthio with 1 or 2 carbon atoms,halogenoalkylthio with 1 or 2 carbon atoms and 1 to 3 chlorine and/orfluorine atoms and furyl and phenyl, which can optionally be mono-, di-or trisubstituted by identical or different substituents from the groupcomprising chlorine and fluorine, or represents cycloalkyl which has 3to 6 carbon atoms and is optionally mono-, di-, tri-, tetra-, penta- orhexasubstituted by identical or different substituents from the groupcomprising fluorine, chlorine, alkyl with 1 or 2 carbon atoms, alkoxywith 1 or 2 carbon atoms, halogenoalkoxy with 1 or 2 carbon atoms and 1to 5 chlorine and/or fluorine atoms, alkylthio with 1 or 2 carbon atomsand halogenoalkylthio with 1 or 2 carbon atoms and with 1 to 3 chlorineand/or fluorine atoms, and

R² represents alkyl with 1 to 3 carbon atoms, alkenyl with 3 or 4 carbonatoms, alkinyl with 3 or 4 carbon atoms, alkoxyalkyl with 1 or 2 carbonatoms in the alkoxy part and 1 to 3 carbon atoms in the alkyl part,alkylthioalkyl with 1 or 2 carbon atoms in the alkylthio part and 1 to 3carbon atoms in the alkyl part, alkoxycarbonylalkyl with 1 or 2 carbonatoms in the alkoxy part and 2 or 3 carbon atoms in the alkyl part orcyanoalkyl with 1 to 3 carbon atoms in the alkyl part.

Especially preferred compounds of the formula (I) are those

in which

Ar represents phenyl which is optionally mono-, di-, tri- ortetrasubstituted by identical or different substituents from the groupcomprising fluorine, chlorine, methyl, ethyl, isopropyl,trichloromethyl, trifluoromethyl, tetrachloroethyl, tetrafluoroethyl,methoxy, ethoxy, propoxy, trifluoromethoxy, difluorochloromethoxy,trifluoromethylthio, fluorosulphonyl, dimethylamino, diethylamino andnitro,

R¹ represents straight-chain or branched alkyl with 1 to 12 carbonatoms, in particular isopropyl, sec.-butyl, tert.-butyl, sec.-pentyl,neopentyl, cyclohexyl, furylmethyl or benzyl and

R² represents straight-chain or branched alkyl with 1 to 3 carbon atoms,in particular methyl or ethyl, or represents cyanomethyl, 2-cyanoethyl,methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl,allyl or propargyl.

If1-(3-trifluoromethoxyphenyl)-3-(2,2-dimethyl-propyl)-1,3,5-triazine-2,4,6-trioneand ethyl iodine are used as starting substances according to processa), the course of the reaction can be illustrated by the followingequation. ##STR7##

If N-(3,5-dichlorophenyl)-N'-allylurea andbischlorocarbonyl-N-methylamine are used as starting substancesaccording to process b), the course of the reaction can be illustratedby the following equation: ##STR8##

If bis-chlorocarbonyl-N-(2,4-dichlorophenyl)-amine andN-methyl-N'-(2,2-dimethylpropyl)-urea are used as starting substancesaccording to process(c), the course of the reaction can be illustratedby the following equation: ##STR9##

Formula (II) provides a general definition of the disubstituted1,3,5-triazine-2,4,6-triones required as starting substances in processa) according to the invention. In this formula, Ar and R¹ preferablyhave the meaning which have already been mentioned in connection withthe description of the substances of the formula (I) according to theinvention.

The 1,3,5-triazine-2,4,6-triones of the general formula (II) are knownin some cases or can be obtained in a manner which is known per se, forexample from N,N'-disubstituted ureas (IV) and chlorocarbonylisocyante(compare Angew. Chem. 89 (1977), 789). The alkylating agents of theformula (III) to be used for process (a) are likewise known. Preferably,in this case, X represents chloride, bromide, iodide or sulphate.

The ureas of the general formulae (IV) and (VI) to be used for processes(b) or (c) according to the invention are known per se and areproducible by addition of isocyanates onto primary amines (compareHouben-Weyl: Methoden der organischen Chemie, [Methods of organicchemistry], volume E 4 (1983) page 352, Thieme-Verlag, Stuttgart).

The bis-chlorocarbonylamines of the general formulae (V) and (VII) to beused in process (b) or (c) are Likewise known (compare Houben-Weyl:Methoden der organischen Chemie, [Methods of organic chemistry], volumeE 4 (1983), page 1022, Thieme-Verlag, Stuttgart).

The reaction temperatures can be varied within a substantial range inthe processes according to the invention. The reaction is carried out ingeneral between 20° C. and 150° C., preferably between 50° C. and 120°C., in process (a) and in general between 0° C. and 150° C., preferablybetween 20° C. and 120° C., in processes (b) and (c).

In carrying out the processes according to the invention, the startingsubstances and if appropriate the acid-binding agents are employed inapproximately equimolar amounts. An excess of acid-binding agents ingeneral does no harm.

The reactions are preferably carried out in the presence of a diluent.Possible diluents are all the inert organic solvents. These include,preferably, hydrocarbons, such as toluene and xylene; chlorinatedhydrocarbons, such as chlorobenzene and chloroform; ketones, such asacetone, ethers, such as tetrahydrofurane and dioxane; and nitriles,such as acetonitrile.

All the customary acid-binding agents can be used as the acid-bindingagents. These include, preferably, tertiary amines, such astriethylamine and pyridine; alkali metal hydroxides, such as sodiumhydroxide and potassium hydroxide, and alkali metal carbonates andbicarbonates, such as potassium carbonate and sodium bicarbonate.

The compounds according to the invention are worked up and isolated inthe customary manner. They are in general obtained immediately ascrystals or remain as crystals after evaporation of the solvent.

The active compounds according to the invention exhibit a powerfulbiological action and can be employed in practice for combatingundesirable pests. The active compounds are suitable for use, forexample, as plant protection agents, above all as fungicides.

Fungicidal agents in plant protection are employed for combatingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deateromycetes.

Some causative organisms of fungal diseases which come under the genericnames listed above may be mentioned as examples, but not by way oflimitation:

Pythium species, such as, for example, Pythium ultimum; Phytophthoraspecies, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera Leucotricha;Venturia species, such as, for example, Venturia inaequalis; Pyrenophoraspecies, such as, for example, Pyrenophora teres or P. graminea (conidiaform: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae; Pellicularia species, such as, for example, Pelliculariasasakii;

Pyricularia species, such as, for example, Pyrisasakii; Pyriculariaspecies, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum; Botrytisspecies, such as, for example, Botrytis cinerea; Septoria species, suchas, for example, Septoria nodorum; Leptosphaeria species, such as, forexample, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae;

and Pseudocercosporella species, such as, for example,Pseudocercosporella herpotrichoides.

The good toleration, by plants, of the active compounds, at theconcentrations required for combating plant diseases, permits treatmentof above-ground parts of plants, of vegetative propagation stock andseeds, and of the soil.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, suspensions, powders, foams, pastes,granules, aerosols, very fine capsules in polymeric substances and incoating compositions for seed, as well as ULV formulations.

These formulations are produced in known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is, emulsifying agents and/or dispersingagents, and/or foam-forming agents. In the case of the use of water asan extender, organic solvents can, for example, also be used asauxiliary solvents. As liquid solvents, there are suitable in the main:aromatics, such as xylene, toluene or alkyl naphthalenes, chlorinatedaromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethylsulphoxide, as well as water. By liquefied gaseous extenders orcarriers are meant liquids which are gaseous at normal temperature andunder normal pressure, for example aerosol propellants, such ashalogenated hydrocarbons as well as butane, propane, nitrogen and carbondioxide. As solid carriers there are suitable: for example groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly-disperse silicic acid, alumina and silicates.As solid carriers for granules there are suitable: for example crushedand fractionated natural rocks such as calcite, marble, pumice,sepiolite and dolomite, as well as synthetic granules of inorganic andorganic meals, and granules of organic material such as sawdust, coconutshells, corn cobs and tobacco stalks. As emulsifying and/or foam-formingagents there are suitable: for example non-ionic and anionicemulsifiers, such as polyoxyethylene-fatty acid esters,polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycolethers, alkyl sulphonates, alkyl sulphates, aryl subphonates as well asalbumin hydrolysis products. As dispersing agents there are suitable:for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be present in theformulations as a mixture with other known active compounds, such asfungicides, insecticides and acaricides, and in mixtures withfertilizers and growth regulators.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, emulsifiable concentrates, emulsions, foams, suspensions,wettable powders, pastes, soluble powders, dusts and granules. They areused in the customary manner, for example by watering, spraying,atomizing, scattering, dusting, foaming, brushing on and the like. It isfurthermore possible to apply the active compounds by the ultra-lowvolume method or to inject the active compound formulation or the activecompound itself into the soil. The seeds of the plants can also betreated.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range. They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.00l%.

In the treatment of seed, amounts of active compound of 0.001 to 50 gper kilogram of seed, preferably 0.01 to 10 g, are generally required.

For the treatment of soil, active compound concentrations of 0.00001 to0.1% by weight, preferably 0.0001 to 0.02% by weight, are required atthe place of action.

PREPARATION EXAMPLES

The preparation of the active compounds according to the invention byprocess (a) can be seen from the following example.

EXAMPLE 1 ##STR10##

5.2 g (0.037 mol) of methyliodide are added dropwise to a solution of10.0 g (0.033 mol) of1-methoxyphenyl)-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4,6-trione in100 ml of absolute acetonitrile and 9 g (0.066 mol) of potassiumcarbonate at room temperature. The reaction mixture is boiled underreflux for 5 hours. After cooling the solid constituents are separatedoff and the mother liquor is concentrated under reduced pressure. Theresidue obtained after stripping off the solvent is ground with coldwater for purification. The resulting crystals are filtered off withsuction and dried. 10.0 g (95% of theory) of1-(4-methoxyphenyl)-3-(2,2-dimethylpropyl)-5-methyl-1,3,5-triazine-2,4,6-trioneare obtained in this manner in the form of crystals of melting point134° C. The substances listed by way of their formulae in the followingTable 1 are also prepared by the method described in Example 1(identical with Example 25).

                                      TABLE 1                                     __________________________________________________________________________     ##STR11##                                        (I)                         Example                                    Physical                           No.    Ar           R.sup.1   R.sup.2      constants                          __________________________________________________________________________            ##STR12##   C.sub.4 H.sub.9                                                                         C.sub.2 H.sub.5                                 2                                          mp.: 82° C.                         ##STR13##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     bp: 196-200° C./ 0.03                                                  mbar                               3                                                                                     ##STR14##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            mp.: 92° C.                 4                                                                                     ##STR15##   C.sub.4 H.sub.9t                                                                        CH.sub.3     mp.: 130° C.                5                                                                                     ##STR16##   C.sub.4 H.sub.9t                                                                        C.sub.2 H.sub.5                                                                            mp.: 158° C.                6                                                                                     ##STR17##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     mp.: 91° C.                 7                                                                                     ##STR18##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            mp.: 96° C.                 8                                                                                     ##STR19##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.3 H.sub.7n                                                                           mp.: 116° C.                9                                                                                     ##STR20##   C.sub.4 H.sub.9t                                                                        CH.sub.3     mp.: 79° C.                 10                                                                                    ##STR21##   C.sub.4 H.sub.9t                                                                        C.sub.2 H.sub.5                                                                            mp.: 70° C.                 11                                                                                    ##STR22##   C.sub.4 H.sub.9t                                                                        C.sub.3 H.sub.7n                                                                           mp.: 90° C.                 12                                                                                    ##STR23##   C.sub.4 H.sub.9t                                                                        C.sub.3 H.sub.7iso                                                                         n.sub.D.sup.20 : 1.495             13                                                                                    ##STR24##   C.sub.4 H.sub.9t                                                                        CH.sub.2CN   mp.: 126° C.                14                                                                                    ##STR25##   C.sub.4 H.sub.9t                                                                        CH.sub.2COOC.sub.2 H.sub.5                                                                 mp.: 82° C.                 15                                                                                    ##STR26##   C.sub.3 H.sub.7iso                                                                      CH.sub.3     mp.: 75° C.                 16                                                                                    ##STR27##   C.sub.3 H.sub.7iso                                                                      C.sub.2 H.sub.5                                                                            mp.: 83° C.                 17                                                                                    ##STR28##   C.sub.3 H.sub.7iso                                                                      C.sub.3 H.sub.7iso                                                                         n.sub.D.sup.20 : 1.492             18                                                                                    ##STR29##   C.sub.3 H.sub.7iso                                                                      CH.sub.2CN   mp.: 165° C.                19                                                                                    ##STR30##   C.sub.3 H.sub.7iso                                                                      CH.sub.2COOC.sub.2 H.sub.5                                                                 n.sub.D.sup.20 : 1.486             20                                                                                    ##STR31##   CH.sub.3  CH.sub.2CHCH.sub.2                                                                         Oil; IR:  1695 cm.sup.-1           21                                                                                    ##STR32##   CH.sub.2CN                                                                              CH.sub.3     mp.: 126° C.                22                                                                                    ##STR33##   C.sub.2 H.sub.5                                                                         CH.sub.3     mp.: 115° C.                23                                                                                    ##STR34##   CH.sub.3                                                                                 ##STR35##   Oil; IR:  1695 cm.sup.-1           24                                                                                    ##STR36##   CH.sub.3  CH.sub.2COOC.sub.2 H.sub.5                                                                 n.sub.D.sup.20 : 1.486             25                                                                                    ##STR37##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     IR: 1685 cm.sup.-1                 26                                                                                    ##STR38##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            IR: 1680 cm.sup.-1                 27                                                                                    ##STR39##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.3 H.sub.7n                                                                           mp.: 86° C.                 28                                                                                    ##STR40##   C.sub.4 H.sub.9t                                                                        CH.sub.3     mp.: 130° C.                29                                                                                    ##STR41##   C.sub.4 H.sub.9t                                                                        C.sub.2 H.sub.5                                                                            mp.: 96° C.                 30                                                                                    ##STR42##   C.sub.4 H.sub.9t                                                                        C.sub.3 H.sub.7n                                                                           mp.: 94° C.                 31                                                                                    ##STR43##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     mp.: 134° C.                32                                                                                    ##STR44##   CH.sub.2C(CH.sub.3).sub. 3                                                              C.sub.2 H.sub.5                                                                            mp.: 118° C.                33                                                                                    ##STR45##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.3 H.sub.7iso                                                                         IR:  1690 cm.sup.-1                34                                                                                    ##STR46##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     mp.: 111° C.                35                                                                                    ##STR47##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            bp.: 170° C./ 0.04                                                     mbar                               36                                                                                    ##STR48##   C.sub.3 H.sub.7iso                                                                      CH.sub.3     IR: 1690 cm.sup.-1                 37                                                                                    ##STR49##   CH.sub.3  CH.sub.2CHCH.sub.2                                                                         mp.: 78° C.                 38                                                                                    ##STR50##   CH.sub.3  CH.sub.2CN   mp.: 175° C.                39                                                                                    ##STR51##   CH.sub.3   CH.sub.2COC.sub.2 H.sub.5                                                                 n.sub.D.sup.20 : 1.482             40                                                                                    ##STR52##   C.sub.2 H.sub.5                                                                         CH.sub.3     mp.: 83° C.                 41                                                                                    ##STR53##   C.sub.4 H.sub.9t                                                                        CH.sub.3     IR: 1680 cm.sup.-1                 42                                                                                    ##STR54##   C.sub.4 H.sub.9t                                                                        C.sub.2 H.sub.5                                                                            IR: 1695 cm.sup.-1                 43                                                                                    ##STR55##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     mp.: 110° C.                44                                                                                    ##STR56##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            mp.: 92° C.                 45                                                                                    ##STR57##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.3 H.sub.7n                                                                           mp.: 108° C.                46                                                                                    ##STR58##   C.sub.4 H.sub.9t                                                                        CH.sub.3     mp.: 96° C.                 47                                                                                    ##STR59##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     Oil; IR:  1695 cm.sup.-1           48                                                                                    ##STR60##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            Oil; IR:  1700 cm.sup.-1           49                                                                                    ##STR61##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.3 H.sub.7n                                                                           Oil; IR:  1698 cm.sup.-1           50                                                                                    ##STR62##   C.sub.4 H.sub.9t                                                                        CH.sub.3     Oil; IR:  1700 cm.sup.-1           51                                                                                    ##STR63##   C.sub.4 H.sub.9t                                                                        C.sub.2 H.sub.5                                                                            Oil; IR:  1700 cm.sup.-1           52                                                                                    ##STR64##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     Oil; IR:  1700 cm.sup.-1           53                                                                                    ##STR65##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            Oil, IR:  1705 cm.sup.-1                                                      (contains chloroform CHCl.sub.3                                               )                                  54                                                                                    ##STR66##   C.sub.4 H.sub.9t                                                                        C.sub.2 H.sub.5                                                                            mp.: 90° C.                 55                                                                                    ##STR67##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     mp.: 112° C.                56                                                                                    ##STR68##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            mp.: 80° C.                 57                                                                                    ##STR69##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     mp.: 83° C.                 58                                                                                    ##STR70##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            mp.: 92° C.                 59                                                                                    ##STR71##   C.sub.4 H.sub.9t                                                                        CH.sub.3     mp.: 82° C.                 60                                                                                    ##STR72##   C.sub.4 H.sub.9n                                                                        CH.sub.3     mp.: 74° C.                 61                                                                                    ##STR73##                                                                                  ##STR74##                                                                              CH.sub.3     mp.: 125° C.                62                                                                                    ##STR75##                                                                                  ##STR76##                                                                              CH.sub.3     Oil; IR:  1690 cm.sup.-1           63                                                                                    ##STR77##                                                                                  ##STR78##                                                                              CH.sub.3     mp.: 146° C.                64                                                                                    ##STR79##   CH.sub.3  CH.sub.3     mp.: 140°  C.               65                                                                                    ##STR80##   C.sub.12 H.sub.25                                                                       CH.sub.3     mp.: 65° C.                 66                                                                                    ##STR81##   C.sub.3 H.sub.7iso                                                                      CH.sub.3     mp.: 98° C.                 67                                                                                    ##STR82##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     mp.: 123° C.                68                                                                                    ##STR83##   C.sub.4 H.sub.9t                                                                        CH.sub.3     mp.: 103° C.                69                                                                                    ##STR84##   C.sub.4 H.sub.9t                                                                        iC.sub.3 H.sub.7                                                                           n.sub.D.sup.20 : 1.485             70                                                                                    ##STR85##   C.sub.4 H.sub.9t                                                                        CH.sub.2CHCH.sub.2                                                                         mp.: 80° C.                 71                                                                                    ##STR86##   C.sub.4 H.sub.9t                                                                        CH.sub.2 CN  mp.: 107° C.                72                                                                                    ##STR87##   C.sub.4 H.sub.9t                                                                        CH.sub.2COOC.sub.2 H.sub.5                                                                 n.sub.D.sup.20 : 1.485             73                                                                                    ##STR88##   C.sub.4 H.sub.9 t                                                                       C.sub.2 H.sub.5                                                                            n.sub.D.sup.20 : 1.490             74                                                                                    ##STR89##   C.sub.4 H.sub.9t                                                                        C.sub.2 H.sub.5                                                                            mp.: 130°  C.               75                                                                                    ##STR90##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            mp.: 108° C.                76                                                                                    ##STR91##   C.sub.12 H.sub.25                                                                       CH.sub.3     mp.: 64° C.                 77                                                                                    ##STR92##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.2 H.sub.5                                                                            mp.: 136° C.                78                                                                                    ##STR93##   C.sub.4 H.sub.9t                                                                        C.sub.2 H.sub.5                                                                            mp.: 104° C.                79                                                                                    ##STR94##   CH.sub.2C(CH.sub.3).sub.3                                                               CH.sub.3     mp.: 146° C.                80                                                                                    ##STR95##   CH.sub.2 C(CH.sub.3).sub.3                                                              C.sub.2 H.sub.5                                                                            mp.: 114° C.                81                                                                                    ##STR96##   CH.sub.2C(CH.sub.3).sub.3                                                               C.sub.3 H.sub.7iso                                                                         mp.: 128° C.                82                                                                                    ##STR97##                                                                                  ##STR98##                                                                              CH.sub.3     mp.: 126° C.                83                                                                                    ##STR99##   C.sub.3 H.sub.7n                                                                        CH.sub.3     mp.: 94° C.                 84                                                                                    ##STR100##  C.sub.4 H.sub.9t                                                                        CH.sub.3     mp.: 122° C.                85                                                                                    ##STR101##  C.sub.3 H.sub.7iso                                                                      CH.sub.3     Oil; IR:  1695 cm.sup.-1           86                                                                                    ##STR102##  CH.sub.3  CH.sub.2CHCH.sub.2                                                                         mp.: 166° C.                87                                                                                    ##STR103##  C.sub.4 H.sub.9t                                                                        CH.sub.3     150-160° C. (decompositi                                               on)                                88                                                                                    ##STR104##  C.sub.4 H.sub.9t                                                                        CH.sub.3     mp.: 130° C.                89                                                                                    ##STR105##  C.sub.3 H.sub.7iso                                                                      CH.sub.3     mp.: 185° C.                __________________________________________________________________________

EXAMPLE 90 (Process b) ##STR106##

12.3 g (0.05 mol) of N(3,5-dichlorophenyl)-N'-allylurea (melting point113-134° C.) are dissolved in 100 ml of dioxane, and 8 g (0.051 mol) ofbis-chlorocarbonyl-N-methylamine are added. On warming, HCL escapescontinuously. The mixture is heated under reflux for 1 hour, until theevolution of gas has ended. 150 ml of water are added to this reactionsolution at room temperature. The reaction product thereby crystallizes.It is filtered off with suction and rinsed with methanol. Yield: 9 g=55%of theory; melting point: 165°-167° C.

The following compounds of the formula ##STR107## are obtained in ananalogous manner:

                  TABLE 2                                                         ______________________________________                                        Example                             Physical                                  No.    Ar          R.sup.1   Alkyl  constants                                 ______________________________________                                        91     3,5 Cl.sub.2 --C.sub.6 H.sub.3                                                            tert.-C.sub.4 H.sub.9                                                                   CH.sub.3                                                                             mp.: 160° C.                       92     3,5 Cl.sub.2 --C.sub.6 H.sub.3                                                            CH.sub.3  CH.sub.3                                                                             mp.: 250° C.                       ______________________________________                                    

EXAMPLE 93 (Process C) ##STR108##

2.5 g (17.4 mmol) of N-methyl-N'-(2,2-dimethylpropyl) urea are dissolvedin 20 ml of dioxane, and 5 g (17.4 mmol) ofbis-chlorocarbonyl-N-2,4-dichlorophenylamine are added. On warming, HCLescapes continuously. The mixture is heated under reflux for 1 hour,until the evolution of gas has ended. 150 ml of ice-water are added tothis solution. The reaction product thereby crystallizes. It is filteredoff with suction and recrystallized in a mixture of toluene andpetroleum ether.

Yield: 2.2 g=35% of theory;

Melting point=110°-112° C.

The following compounds of the formula ##STR109## are obtained in ananalogous manner.

                                      TABLE 3                                     __________________________________________________________________________    Ex-                                                                           am-                                                                           ple                                                                           No.                                                                              Ar                 R.sup.1       R.sup.2   Physical Constants              __________________________________________________________________________     94                                                                               ##STR110##        C(CH.sub.3).sub.3                                                                           CH.sub.3  m.p.: 110° C.             95                                                                               ##STR111##        C(CH.sub.3).sub.3                                                                           C.sub.3 H.sub.7                                                                         .sup.1 H.sup.CDCL.sbsp.3 :                                                    7.48d(2H; J=8Hz); 7.23d(2H;                                                   J=8Hz); 3.88dd(2H; J=7+6Hz)                                                   .74s(9H); 1.73m(2H);                                                          1.00t(3H; J=7Hz)                 96                                                                               ##STR112##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 92° C.              97                                                                               ##STR113##        C(CH.sub.3).sub.3                                                                           CH.sub.3  .sup.1 H.sup.CDCl :                                                           7.46d(2H; J=8Hz); 7.17d                                                       (2H; J=8Hz); 3.34s(3H);                                                       1.72s(9H)                        98                                                                               ##STR114##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 114° C.             99                                                                               ##STR115##        C(CH.sub.3).sub.3                                                                           CH.sub.4  m.p.: 152° C.            100                                                                               ##STR116##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 110° C.            101                                                                               ##STR117##        C.sub.2 H.sub.5                                                                             CH.sub.3  m.p.: 122° C.            102                                                                               ##STR118##        C.sub.2 H.sub.5                                                                             CH.sub.2CHCH.sub.2                                                                      m.p.: 78° C.             103                                                                               ##STR119##        C(CH.sub.3)   C.sub.2 H.sub.5                                                                         m.p.: 130° C.            104                                                                               ##STR120##        C(CH.sub.3)   CH.sub.3  m.p.: 130° C.            105                                                                               ##STR121##        CH.sub.2C(CH.sub.3).sub.3                                                                   CH.sub.3  m.p.: 111° C.            106                                                                               ##STR122##        C(CH.sub.3).sub.2CH.sub.2OCH.sub.3                                                          C.sub.2 H.sub.5                                                                         m.p.: 86° C.             107                                                                               ##STR123##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         .sup.1 H.sup.DMSO :                                                           7.85d(1H;                                                                     J=2Hz); 7.25dbr(1H; J=8Hz);                                                   7.53dd(1H; J=2+8Hz);                                                          3.79q(2H;                                                                     J=7Hz); 1.65s(9H);                                                            1.16t(3H; J=7Hz)                108                                                                               ##STR124##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         .sup.1 H.sup.CDCL.sbsp.3 :                                                    7.42m(4H);  3.97q(2H;                                                         J=7Hz); 1.74s(9H); 1.28t(3H;                                                   J=7Hz)                         109                                                                               ##STR125##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         .sup.1 H.sup.DMSO :                                                           7.83sbr(1H); 7.77d (1H;                                                       J=8Hz); 7.57dbr(1H; J=8Hz);                                                   .82q(2H; J=7Hz); 1.64s(9H);                                                   .16t(3H; J=7Hz)                 110                                                                               ##STR126##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 61° C.             111                                                                               ##STR127##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 102° C.            112                                                                               ##STR128##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         IR: 1695 cm.sup.-1              113                                                                               ##STR129##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         IR: 1698 cm.sup.-1              114                                                                               ##STR130##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         IR: 1690 cm.sup.-1              115                                                                               ##STR131##        C.sub.2 H.sub.5                                                                             C.sub.2 H.sub.5                                                                         m.p.: 116° C.            116                                                                               ##STR132##        C(CH.sub.3).sub.2C.sub.2 H.sub.5                                                            C.sub.2 H.sub.5                                                                         .sup.1 H.sup.DMSO :                                                           7.47,(4H); 3.78q(2H;                                                          J=7Hz); 2.03q(2H; J=7Hz);                                                     1.58s (6H); 1.15t(3H;                                                         J=7Hz); 0.85t (3H; J=7Hz)       117                                                                               ##STR133##        C(CH.sub.3).sub.2CH.sub.2C(CH.sub.3).sub.3                                                  C.sub.2 H.sub.5                                                                         IR: 1692 cm.sup.-1              118                                                                               ##STR134##        CH.sub.2CH.sub.2C(CH.sub.3).sub.3                                                           C.sub.2 H.sub.5                                                                         m.p.: 108° C.            119                                                                               ##STR135##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         IR: 1695 cm.sup.-1              120                                                                               ##STR136##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 108° C.            121                                                                               ##STR137##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 94° C.             122                                                                               ##STR138##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 112° C.            123                                                                               ##STR139##        C(CH.sub.3).sub.3                                                                           C.sub. 2 H.sub.5                                                                        m.p.: 96° C.             124                                                                               ##STR140##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 92° C.             125                                                                               ##STR141##        C(CH.sub.3).sub. 3                                                                          C.sub.2 H.sub.5                                                                         IR: 1685 cm.sup.-1              126                                                                               ##STR142##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         .sup.1 H.sup.DMSO :                                                           7.69d(1H; J=8Hz); 7.60d(1H;                                                   J=2Hz); 7.45dd(1H; J=2+8Hz);                                                   7.37dt(1H; J=46+4,5Hz);                                                      3.80qbr(2H; J=7Hz);                                                           1.63s(9H); 1.17t(3H;                                                          J=7Hz)                          127                                                                               ##STR143##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         .sup.1 H.sup.CDCl.sbsp.3 :                                                    7.82d(1H;                                                                     J=2Hz); 7.66dd(1H;                                                            J=8+2Hz); 7.47d (1H;                                                          J=8Hz); 3.97q(2H; J=7Hz);                                                     1.70s(9H); 1.28t(3H;                                                          J=7Hz)                          128                                                                               ##STR144##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 154° C.            129                                                                               ##STR145##        C.sub.4 H.sub.9                                                                             C.sub.2 H.sub.5                                                                         m.p.: 92° C.             130                                                                               ##STR146##        CH(CH.sub.3)C.sub.2 H.sub.5                                                                 C.sub.2 H.sub.5                                                                         .sup.1 H.sup.CDCl.sbsp.3 :                                                    7.33m(4H); 4.82sextett (1H;                                                   J=7Hz); 4.00q(2H; J=7Hz);                                                     2.07quintett d(1H;                                                            J=7+17Hz); 1.84quintett                                                       d(1H; J=7+17Hz); 1.48d(3H;                                                    J=7Hz); 1.29t(3H; J=7Hz);                                                     0.91t(3H; J=7Hz)                131                                                                               ##STR147##        CH.sub.2CF.sub.3                                                                            C.sub.2 H.sub.5                                                                         m.p.: 116° C.            132                                                                               ##STR148##        CH.sub.2CF.sub.3                                                                            CH(CH.sub.3).sub.2                                                                      IR: 1695 cm.sup.-1              133                                                                               ##STR149##                                                                                       ##STR150##   CH.sub.3  m.p.: 98° C.             134                                                                               ##STR151##                                                                                       ##STR152##   C.sub.2 H.sub.5                                                                         m.p.: 78° C.             135                                                                               ##STR153##        C(CH.sub.3).sub.3                                                                           CH.sub.2CHCH.sub.2                                                                      m.p.: 68° C.             136                                                                               ##STR154##        C(CH.sub.3).sub.3                                                                           CH.sub.2CCH                                                                             m.p.: 110° C.            137                                                                               ##STR155##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 150° C.            138                                                                               ##STR156##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 94° C.             139                                                                               ##STR157##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 100° C.            140                                                                               ##STR158##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         IR: 1680 cm.sup.-1              141                                                                               ##STR159##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 64° C.             142                                                                               ##STR160##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 114° C.            143                                                                               ##STR161##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 104° C.            144                                                                               ##STR162##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         IR: 1692 cm.sup.-1              145                                                                               ##STR163##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         m.p.: 102° C.            146                                                                               ##STR164##        C(CH.sub.3).sub.3                                                                           C.sub.2 H.sub.5                                                                         IR: 1690 cm.sup.-1              147                                                                               ##STR165##                                                                                       ##STR166##   CH.sub.3  m.p.: 116° C.            148                                                                               ##STR167##                                                                                       ##STR168##   C.sub.2 H.sub.5                                                                         m.p.: 106° C.            149                                                                               ##STR169##                                                                                       ##STR170##   CH(CH.sub.3).sub.2                                                                      IR: 1695 cm.sup.-1              150                                                                               ##STR171##        C(CH.sub.3).sub.3                                                                           CH.sub.3  m.p.: 112° C.            151                                                                               ##STR172##        C(CH.sub.3).sub.3                                                                           CH.sub.2CHCH.sub.2                                                                      m.p.: 114° C.            152                                                                               ##STR173##        C(CH.sub.3).sub.3                                                                           C.sub.3 H.sub.7                                                                         IR: 1690 cm.sup.-1              153                                                                               ##STR174##        CH(CH.sub.3).sub.2                                                                          C.sub.2 H.sub.5                                                                         m.p.: 104° C.            154                                                                               ##STR175##        CH(CH.sub.3).sub.2                                                                          CH(CH.sub.3).sub.2                                                                      m.p.: 120° C.            155                                                                               ##STR176##        CH(CH.sub.3).sub.2                                                                          C.sub.3 H.sub.7                                                                         m.p.: 112°  C.           156                                                                               ##STR177##        CH(CH.sub.3).sub.2                                                                          CH.sub.2CHCH.sub.2                                                                      m.p.: 124° C.            157                                                                               ##STR178##        C(CH.sub.3).sub.3                                                                           CH.sub.3  m.p.: 89° C.             158                                                                               ##STR179##        C(CH.sub.3).sub.3                                                                           CH.sub.2CHCH.sub.2                                                                      m.p.: 70° C.             159                                                                               ##STR180##        C(CH.sub.3).sub.3                                                                           C.sub.3 H.sub.7                                                                         m.p.: 66° C.             160                                                                               ##STR181##        CH(CH.sub.3).sub.3                                                                          CH.sub.3  m.p.: 118° C.            161                                                                               ##STR182##        C(CH.sub.3).sub.3                                                                           CH.sub.3  m.p.: 142° C.            162                                                                               ##STR183##        C(CH.sub.3).sub.3                                                                           CH.sub.2CHCH.sub.2                                                                      m.p.: 78° C.             163                                                                               ##STR184##        C(CH.sub.3).sub.3                                                                           CH.sub.2CHCH.sub.2                                                                      m.p.: 82° C.             164                                                                               ##STR185##        C(CH.sub.3).sub.3                                                                           CH.sub.3  IR: 1680 cm.sup.-1              165                                                                               ##STR186##        C(CH.sub.3).sub.3                                                                           C.sub.3 H.sub.7                                                                         m.p.: 70° C.             166                                                                               ##STR187##        C(CH.sub.3).sub.3                                                                           CH.sub.2CHCH.sub.2                                                                      m.p.: 90° C.             167                                                                               ##STR188##        C(CH.sub.3).sub.3                                                                           CH.sub.3  m.p.: 126° C.            168                                                                               ##STR189##        C(CH.sub.3).sub.3                                                                           C.sub.3 H.sub.7                                                                         m.p.: 84° C.             169                                                                               ##STR190##        C(CH.sub.3).sub.3                                                                           CH.sub.2CHCH.sub.2                                                                      m.p.: 92° C.             170                                                                               ##STR191##                                                                                       ##STR192##   CH.sub.2CHCH.sub.2                                                                      m.p.: 106° C.            __________________________________________________________________________

USE EXAMPLES Example A

Pyricularia test (rice)/protective

Solvent: 12.5 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water and the stated amount of emulsifier,to the desired concentration.

To test for protective activity, young rice plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated with an aqueous sporesuspension of Pyricularia oryzae. The plants are then placed in agreenhouse at 100% relative atmospheric humidity and 25° C.

Evaluation of the disease infestation is carried out 4 days after theinoculation.

In this test, for example, a clearly superior activity compared with theprior art is shown by the compounds according to Preparation Examples 1,9, 10,14, 29, 30, 37, 54, 68, 73 and 78.

Example B

Pyricularia test (rice)/systemic

Solvent: 12.5 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water and the stated amount of emulsifier,to the desired concentration.

To test for systemic properties, standard soil in which young riceplants have been grown is watered with 40 ml of the preparation ofactive compound. 7 days after the treatment, the plants are inoculatedwith an aqueous spore suspension of Pyricularia oryzae. Thereafter, theplants remain in a greenhouse at a temperature of 25° C. and a relativeatmospheric humidity of 100% until they are evaluated.

Evaluation of the disease infestation is carried out 4 days after theinoculation.

In this test, for example, a clearly superior activity compared with theprior art is shown by the compounds according to Preparation Examples 1,9, 10,29, 30, 54, and 78.

It will be appreciated that the instant specification and examples areset forth by way of illustration and not limitation, and that variousmodifications and changes may be made without departing from the spiritand scope of the present invention.

What is claimed is:
 1. A trisubstituted 1,3,5-triazine-2,4,6-trione ofthe formula ##STR193## in which Ar represents phenyl, which is mono-,di-, tri-, tetra- or pentasubstituted by identical or differentsubstituents from the group comprising halogen, alkyl with 1 to 4 carbonatoms, halogenoalkyl, with 1 to 4 carbon atoms and 1 to 5 identical ordifferent halogen atoms, alkoxy with 1 to 4 carbon atoms, halogenoalkoxywith 1 to 4 carbon atoms and 1 to 5 identical or different halogenatoms, alkylthio with 1 to 4 carbon atoms, halogenoalkylthio with 1 to 4carbon atoms and 1 to 5 identical or different halogen atoms,halogenosulphonyl, dialkylamino with identical or differentstraight-chain or branched alkyl radicals with in each case 1 to 4carbon atoms or nitro,R¹ represents straight-chain or branched alkylwhich has 1 to 12 carbon atoms and is optionally mono- orpolysubstituted by identical or different substituents from the groupcomprising alkoxy with 1 to 3 carbon atoms, halogenoalkoxy with 1 or 2carbon atoms and 1 to 5 identical or different halogen atoms, alkylthiowith 1 to 3 carbon atoms, halogenoalkylthio with 1 or 2 carbon atoms and1 to 5 identical or different halogen atoms and furyl and phenyl, whichcan likewise be mono-, di-, tri-, tetra- or pentasubstituted byidentical or different halogen atoms; or represents cycloalkyl which has3 to 8 carbon atoms and is optionally mono-, di-, tri-, tetra-, penta-or hexasubstituted by identical or different substituents from the groupcomprising halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 3carbon atoms, halogenoalkoxy with 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, alkylthio with 1 to 3 carbon atomsand halogenoalkylthio with 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, and R² is different from R¹ and representsalkyl with 1 to 4 carbon atoms, alkenyl with 3 to 5 carbon atoms,alkinyl with 3 to 5 carbon atoms, alkoxyalkyl with in each case 1 to 3carbon atoms in the alkoxy part and in the alkyl part, alkylthioalkylwith in each case 1 to 3 carbon atoms in the alkylthio part and in thealkyl part of alkoxycarbonylalkyl with 1 to 3 carbon atoms in the alkoxypart and 2 or 3 carbon atoms in the alkyl part, or represents cyanoalkylwith 1 to 5 carbon atoms in the alkyl part.
 2. A trisubstituted1,3,5-triazine-2,4,6-trione according to claim 1,in which Ar representsphenyl, which is mono-, di-, tri-, or tetrasubstituted by identical ordifferent substituents from the group comprising fluorine, chlorine,bromine, alkyl with 1 to 3 carbon atoms, halogenoalkyl with 1 to 3carbon atoms and 1 to 5 chlorine and/or fluorine atoms, alkoxy with 1 to3 carbon atoms, halogenoalkoxy with 1 or 2 carbon atoms and 1 to 5chlorine and/or fluorine atoms, alkylthio with 1 or 2 carbon atoms,halogenoalkylthio with 1 to 3 carbon atoms and 1 to 5 chlorine and/orfluorine atoms, fluorosulphonyl, dialkylamino with identical ordifferent straight-chain or branched alkyl radicals with in each case 1to 3 carbon atoms or nitro, R¹ represents straight-chain or branchedalkyl which has 1 to 12 carbon atoms and can be mono-, di-, ortrisubstituted by identical or different substituents from the groupcomprising alkoxy with 1 or 2 carbon atoms, halogenoalkoxy with 1 or 2carbon atoms and 1 to 3 chlorine and/or fluorine atoms, alkylthio with 1or 2 carbon atoms, halogenoalkythio with 1 or 2 carbon atoms and 1 to 3chlorine and/or fluorine atoms and furyl and phenyl, which canoptionally be mono-, di- or trisubstituted by identical or differentsubstituents from the group comprising chlorine and fluorine, orrepresents cycloalkyl which has 3 to 6 carbon atoms and is optionallymono-, di-, tri-, tetra-, penta- or hexasubstituted by identical ordifferent substituents from the group comprising fluorine, chlorine,alkyl with 1 or 2 carbon atoms, alkoxy with 1 or 2 carbon atoms,halogenoalkoxy with 1 or 2 carbon atoms and 1 to 5 chlorine and/orfluorine atoms, alkylthio with 1 or 2 carbon atoms and halogenoalkylthiowith 1 or 2 carbon atoms and with 1 to 3 chlorine and/or fluorine atoms,and R² is different from R¹ and represents alkyl with 1 to 3 carbonatoms, alkinyl with 3 or 4 carbon atoms, alkenyl with 3 or 4 carbonatoms, alkoxyalkyl with 1 or 2 carbon atoms in the alkoxy part and 1 to3 carbon atoms in the alkyl part, alkylthioalkyl with 1 or 2 carbonatoms in the alkylthio part and 1 to 3 carbon atoms in the alkyl part,alkoxycarbonylalkyl with 1 or 2 carbon atoms in the alkoxy part and 2 or3 carbon atoms in the alkyl part of cyanoalkyl with 1 to 3 carbon atomsin the alkyl part.
 3. A trisubstituted 1,3,5-triazine-2,4,6-trionesaccording to claim 1,in which Ar represents phenyl which is mono-, di-,tri- or tetrasubstituted by identical or different substituents from thegroup comprising fluorine, chlorine, methyl, ethyl, isopropyl,trichloromethyl, trifluoromethyl, tetrachloroethyl, tetrafluoroethyl,methoxy, ethoxy, propoxy, trifluoromethoxy, difluorochloromethoxy,trifluoromethylthio, fluorosulphonyl, chlorosulphonyl, dimethylamino,diethylamino and/or nitro, R¹ represents straight-chain or branchedalkyl with 1 to 12 carbon atoms, or represents cyclohexyl, furylmethylor benzyl, and R² is different from R¹ and represents straight-chain orbranched alkyl with 1 to 5 carbon atoms, or represents cyanomethyl,2-cyanoethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,n-propoxycarbonylmethyl, allyl or propargyl.
 4. A compound according toclaim 1, wherein such compound is1-(4-trifluoromethoxyphenyl)-3-t-butyl-5-methyl-1,3,5-triazine-2,4,6-trioneof the formula ##STR194##
 5. A compound according to claim 1, whereinsuch compound is1-(4-trifluoromethoxyphenyl)-3-t-butyl-5-ethyl-1,3,5-triazine-2,4,6-trioneof the formula ##STR195##
 6. A compound according to claim 1, whereinsuch compound is1-(4-ethoxyphenyl)-3-t-butyl-5-ethyl-1,3,5-triazine-2,4,6-trione of theformula ##STR196##
 7. A compound according to claim 1, wherein suchcompound is1-[4-(1,1,2,2-tetrafluoroethyl)-phenyl]-3-t-butyl-5-ethyl-1,3,5-triazine-2,4,6-trioneof the formula ##STR197##
 8. A fungicidal composition comprising afungicidally effective amount of a compound according to claim 1 and adiluent.